


In Which Dean Winchester Discovers His B Side

by nochick_fics



Category: Supernatural
Genre: Alternate Universe, Alternate Universe - Modern Setting, M/M, Slash, Supernatural AU - Freeform
Language: English
Status: Completed
Published: 2013-11-09
Updated: 2013-11-09
Packaged: 2017-12-31 22:45:03
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 5,105
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1037256
Author URL: https://archiveofourown.org/users/nochick_fics/pseuds/nochick_fics
Summary: <blockquote class="userstuff">
              <p>Dean winds up at a bar called Purgatory and makes a brand new friend.</p>
            </blockquote>





	In Which Dean Winchester Discovers His B Side

**Author's Note:**

> I think there are two reasons I felt so overwhelmingly compelled to write this.  1. Benny and Dean <3\.  2. In the short time I've been into Supernatural, I've been very intrigued by all the hoopla surrounding Dean's sexual orientation and the strong canon evidence that points towards the possibility of his bisexuality.  I'm not going to get into a whole thing here because it's already been discussed to death everywhere else. Basically, I just wanted to write a fic from his POV that dealt with how he might react to that sort of realization.  Plus... all the sex with Benny.  ;-)
> 
> Originally posted to LiveJournal on 10/28/13.

Dean Winchester knew that he wasn’t gay. No way, no how, absolutely not. Over the years he had slept with more women than he could count, thus proving his irrefutable love of the ladies.

However, he was beginning to suspect that he might not be all that straight, either.

It all started about a month ago. While his brother Sam was out on a date, Dean had decided to use the opportunity to rub one out because he was bored and alone and why the hell not? So he went to it, doing his thing, when all of a sudden the busty Asian beauty he was imagining on his dick morphed into a hung Asian hottie instead. Dean was horrified as hell at the mental transformation… and so turned on that he came all over himself almost immediately.

Afterwards, all he could do was lie there and try to digest the fact that he had just gotten off while thinking about a dude.

A fucking dude. With a dick and everything. _What the hell?_

In the weeks that followed, he tried his damnedest to pretend that it didn’t happen, stepping up his efforts by making the girls swoon more than usual and reestablishing his heretofore undeniable heterosexuality. Except that he was beginning to notice things now, things he hadn’t noticed before. At least not consciously. Like just how good the cashier guy at the convenience store always smelled and how the fellow at the corner bakery always managed to touch his hand when he gave him his pie and the appreciative glance of a random male passerby. All those little instances wore away at Dean’s mind, picking at it like a scab, until he decided to treat the perplexing situation like any other obstacle and confront it head on.

Okay then. So he was possibly… probably… into men. Just a little bit.

There was only one way to find out for sure.

Which was why he was now sitting in the parking lot of a backwoods dive called Purgatory, trying to work up the nerve to get out of the Impala and go inside. He had driven some fifty miles out of the way to get there, far enough- he hoped- to avoid being spotted by anyone who might have recognized him. Dean had discovered the place after doing a Google search for gay bars at the library (not that Sam would have ever checked his laptop browser history but fuck if he was going to take the chance). And now, there he was, watching as men wandered in and out of the establishment and wondering if he was really up for the challenge of finding a means to scratch a most unexpected itch. Because picking up women was one thing, and Dean considered himself a pro at doing it. But this? This was different. And he didn’t have the first fucking clue what to do.

Oh well. He hadn’t come this far just to wimp out now. All he could do was walk inside, get a drink, and play the rest by ear.

Dean got out of the car and pocketed his keys, and then made his way inside, walking past a trio of biker types hovering by the door and eyeballing him like they hadn’t had a meal in weeks. Purgatory was just as gritty on the inside as it was out but Dean had to give props where props were due when the sound of Boston hit his ears. And while he obviously hadn’t expected to walk in and find everyone going to town on the tables (although the thought crossed his mind), Dean was still a bit stunned to see that the bar was like any other, save for the lack of women. Just a bunch of guys sitting around and getting drunk and having a grand old time.

Feeling even more emboldened, he stepped up to the bar and sat down on a stool that had seen better days. After ordering a beer from a bartender who for some reason reminded him of his Uncle Bobby, Dean pretended to give a damn about the football highlights playing on the television and discreetly checked out his options. He didn’t really know what he was looking for because he had never stopped to contemplate his “type” before, and didn’t know what that “type” would even be. Except for hung Asian hotties, apparently. But the night was young and the beer was cheap, so he decided not to sweat it just yet.

Two drinks and some Lynyrd Skynyrd later, Dean sensed a man sitting down, two rickety stools away. He turned to glance at the stranger, not really expecting to see anything he liked… and was instantly taken aback by the most stunning blue eyes he had ever seen. He immediately turned back to the TV and took a long swig of beer, not because he was thirsty but to camouflage his gaping mouth.

Those eyes… holy shit. And Dean was no stranger to gorgeous eyes, being in possession of some lovely green peepers himself. But still… _damn_.

He tried to appear casual, tapping his fingers against the bar top in tune to “Carry on Wayward Son” while trying to recall what the rest of the stranger had looked like in the few seconds their eyes had met.

He was older, late thirties, _maybe_ early forties. He had a beard, brown like his hair, with a sprinkling of grey around the chin. He was a bigger guy. Not fat, but muscular. Solid. And if Dean wasn’t mistaken, he was wearing a pea coat, an odd but interesting choice in that neck of the woods.

By all rights, he looked like the last type of guy that Dean thought he would find attractive. Yet, as it turned out, he was the only man in Purgatory who had captured his attention.

So what was he supposed to do now?

Hitting on girls had always been easy for him. Hell, more often than not, something as insignificant as a commentary on the weather had resulted in some backseat affection. But somehow he did not believe either that or the whole is-Heaven-missing-an-angel line would work on this guy. Or any guy, for that matter.

In the end, Dean decided to take a more direct approach. And so he turned to the ruggedly handsome man with the fuck me eyes and uttered a very simple:

“Hello.”

The man looked at Dean and nodded in greeting. “Evening.”

… Okay, now what?

Fortunately for Dean, his new bar mate got the ball rolling for him.

“Haven’t seen you around here before.”

His voice was low and a little bit gruff, with a slight Louisiana drawl that Dean found to be almost as sexy as his eyes.

“First time,” he responded calmly before taking another sip of his beer. So far, so good.

The man nodded as if he suspected as much. “Welcome to Purgatory.”

He reached over and tapped his bottle to Dean’s and then took a drink of his own.

“Benny,” he said, offering his hand.

While Dean originally had every intention of using an alias that night as a just in case, he felt inexplicably compelled to tell the truth. And why the hell not? It wasn’t as if he had to see him again after tonight.

“Dean.”

Benny’s hand was strong, rough, the kind of hand that knew hard work. Dean liked the way it felt. And he couldn’t help but wonder how it would feel wrapped around his-

“So do you live around here?” he asked quickly, severing his own train of thought before it got out of control.

“For now,” Benny replied. “What about you?”

“I’m from… out of town.”

“Out of town, huh?” The older man raised a brow, unconvinced. “And you decided to come _here_?”

Dean chuckled at the implication, that someone would drive any significant amount of distance to go to Purgatory of their own free will. But he concluded that the place really wasn’t all that bad. Then again, maybe that was the alcohol talking. Or the effect the present company was having on him.

“I suppose I did,” he answered, polishing off the rest of his beer.

“Hm.” Benny regarded him for a moment, his eyes narrowed in a questioning gaze. “Girlfriend or married?” he finally asked.

The question did not bother Dean at all. In fact, if he were in Benny’s shoes, he would have very likely made a presumption along those same lines.

“Neither,” he responded. “I’m just…”

Dean paused and looked Benny in the eyes. Then he sighed and shook his head, his desire to be honest and forthright once again taking hold.

“Man, I’m just trying to figure it out.”

Now Dean wasn’t much of a talker. Never had been and never would be. But even just to utter that one simple yet monumental statement, to verbally acknowledge the dilemma that had plagued him for the better part of a month, it felt… kind of good.

Benny nodded in understanding. “I hear ya, brother.”

He noticed Dean’s empty bottle and finished the rest of his own.

“Another one?” he offered.

Dean reached into his pocket for his wallet and was stopped by a strong arm holding his still.

“I got this round,” Benny said. He motioned for the bartender… and then calmly slid to the stool beside Dean’s, closing the distance between them. “Next one’s on you.”

*****

Three rounds later, Dean had come to realize two things. First off, he had to piss like nobody’s business, and so he excused himself, leaving Benny to his drink, and weaved through the maze of tables and down a dimly lit hallway until he found the small bathroom that was not going to win any prizes for cleanliness anytime soon.

The second thing he realized was that he actually _liked_ this Benny guy. Dean was not the type who made friends easily; the fact that Sam was pretty much his only friend in the world served as proof of that. But beneath the gruff exterior, Benny was the kind of person he wouldn’t have minded getting to know a little better. He spoke his mind and he didn’t ask too many questions, and for a man like Dean, who kept everything close to the vest, it was refreshing to come across someone who didn’t mince words or need to know exactly what he was thinking or feeling.

Oh, there was still the physical attraction. The whole time they sat and talked about things that hardly mattered, Dean was all too aware of the way Benny’s arm rested alongside his, and the man’s eyes and voice were both driving him all kinds of crazy. But lust aside, he was glad to have met someone he was interested in outside of his need to get laid.

He finished up and checked his reflection in the mirror that was in desperate need of Windex. Not bad. Not bad at all.

After that, he opened the door to leave the bathroom and almost walked right into Benny.

“Sorry about that,” he muttered.

“Don’t worry about it,” Benny drawled.

And maybe it was the way that Benny was looking at him or the tone of his voice, but whatever it was, it got Dean’s attention. He met the other man’s gaze in the doorway, not entirely convinced that he was there for the usual reason.

“... Do you _really_ need to take a piss?” he asked, skeptical and hoping.

“Oh, I’m sure I will at _some_ point tonight.” Benny took a step closer, not exactly blocking the doorway but making it very difficult for Dean to leave without brushing up against him.

It was all on Dean now, the ball was in his court. What happened next was completely up to him. And while there was a tiny part of him, way deep down, that wanted to try and take it all back before it was too late, before it became _real_ , he already knew that the time had long passed for him to reconsider what he was about to do.

He wanted this.

He _needed_ this.

And, if only just this once, he wasn’t going to deny it.

Dean moved back. And waited.

With his lips curved in a smirk, Benny stepped inside the bathroom, closing and locking the door behind him.

“Won’t have much time,” he informed him as he peeled off his coat and carefully laid it across the sink.

Just as Dean was about to agree, he got his first good, long, head-to-toe look at Benny. And again, all he could think was _damn_.

“Yeah... I don’t think that’s gonna be a problem.”

Benny grinned and walked towards Dean, moving in slow until he was right up on him. Dean’s alpha instinct threatened to kick in and he had to remind himself that this wasn’t some sort of pissing contest. This was about self-discovery and feeling good and hopefully extinguishing a fire that had been burning for much longer than he was ready to admit. Keeping that in mind, he allowed his body to relax and let the other man gently push him against the wall.

The coolness of the tiles had nothing on the heat emanating from Benny’s body, a heat that permeated Dean’s jacket and shirt and shot right to the bare skin underneath. A part of Dean’s brain was wrestling with the fact that he was about to let a man touch him but the part of his mind that was calling the shots was perfectly fine with letting the show go on.

Benny leaned forward, piercing blue eyes locked on green. He stopped for a moment, as if considering his next move, giving Dean just enough time to steel himself for being kissed by a man.

But Benny didn’t kiss him. At least not on the lips. Instead, he nudged his face into the crook of Dean’s neck, burrowing until he clamped down on a patch of skin. And then he started to suck.

Dean threw back his head and gasped at the contrast of soft lips and a scratchy beard against his skin, sending jolts of pleasure spreading throughout his body. It felt better than he could have imagined, better than he could have ever described. A thigh pressed against him, parting his legs and making a hard situation even harder. Dean moaned and twisted his hands in Benny’s shirt, pulling him closer as he rubbed himself against the firm muscle of the other man’s leg, grinding on it without the first ounce of shame. Benny worked his way along Dean’s neck while the young man rode his leg, licking and sucking and carefully biting him all over, and it occurred to Dean that he was a good minute away from coming in his pants. Two, if he was lucky.

“Wait,” he whispered harshly, and just barely able to manage that.

Benny lowered his leg and pulled back, bracing himself on hands that were planted on the wall behind Dean.

“Second thoughts?” he asked.

Dean shook his head. “No, it’s just…”

He shook his head again, his face growing warm as he tried to think of an eloquent way to explain that he was dangerously close to needing a change of underwear. But Benny was no fool and he quickly understood what Dean was getting at.

“Gotcha,” he said, taking no great pains to hide his amusement.

“Shut up.” Dean smiled as well, even though it was at his own expense.

Benny’s hands trailed over his shoulders and down his chest and stomach, palm side down and fingers splayed over his shirt. Dean tensed, not because he didn’t like it but because he had a very good idea of what was about to happen next.

He swallowed hard as Benny made short work of unzipping his jeans and pushing them down along with his underwear, which was indeed a tad bit damp already.

When Benny spit in his hand and wrapped it around him, his palm and his fingers slick and rough around Dean’s full shaft, it felt every single bit as good as Dean had tried not to imagine earlier. A loud moan that he barely recognized as his own filled the small space as Benny began to stroke him fast and rough. It didn’t take long, as much as Dean tried to hold out. And as he came with a shudder and a sharp cry, clinging to Benny and fucking up hard into his fist, he thought that it really didn’t get much better than a handjob in a dive bar bathroom while the muffled sound of kickass classic rock filtered into the room.

Dean fell against the wall, hunched over and panting from release.

“Damn,” he sighed, still trying to catch his breath.

“You’re welcome,” Benny replied with pretend smugness.

They shared a laugh as Benny washed the cum from his hand and then gave Dean a wad of paper towels to clean himself up. After that, Dean zipped up and waited for the guilt and revulsion to creep in. Now that he had blown his load and was thinking a little more clearly, he figured regret would be a given. Only it wasn’t.

“Alright then.” Benny slipped into his coat. “I could use another drink.”

“What?”

Dean stared at the other man as if trying to solve a problem. He had felt what was going on between Benny’s legs, digging into his hip, firm and urgent. Was he really not expecting any sort of reciprocation for what had just taken place?

“You don’t owe me nothing, Dean.”

Apparently not.

“This ain’t tit for tat,” Benny told him. “I did that because I wanted to.”

“Yeah, but…”

“My hand works just fine. As you know.”

Dean stopped him as he reached for the doorknob, grabbing onto his coat to keep him from leaving. He could hear voices in the hallway, growing louder and headed their way, so sticking around would not be an option. But he wasn’t quite ready to call it a night, either.

“You got somewhere we can go?”

“... You sure?” Benny asked.

Dean nodded. “Yeah.”

“Okay.” Benny smiled. “Follow me.”

*****

The place had four walls, a window, and a bed. That was about it.

“It ain’t much,” Benny explained as he shrugged off his coat and kicked off his boots. “But then again, I don’t need much.”

Dean was hardly surprised. He gathered from their earlier conversation that the man wasn’t the type to stay too put for too long.

“Works for me,” he said, taking a seat on the edge of the unmade bed. “At first, I thought you planned on taking me as far as that contraption you call a truck.”

“Hey now, quit knocking my ride.”

Dean could hear the humor in Benny’s voice as the other man walked over to a small mini-fridge and grabbed two beers, and he was glad all over again to have met someone with whom he had such good rapport.

“I can’t believe that thing is street legal.”

Benny handed him a bottle and sat down beside him, close but not too close. “Well, when you know the right people…”

Dean nodded in agreement. He knew all too well about knowing the right people when it came to cars, considering the few times the old Impala had magically passed inspection when it probably shouldn’t have.

They drank in comfortable silence, feeling no need for unnecessary talk, content with enjoying the sound of nothing and the presence of one another. After a while, Dean pulled out his cell phone and sent Sam a text. He thought it better to get that out of the way now than to have the phone interrupt him later.

“I’m just letting my brother know that I won’t be coming home tonight,” he explained.

“Oh?”

Their eyes locked as the meaning behind Dean’s words hung in the air.

“I take it you’ve figured it out then?” Benny asked.

“I’m still working on it,” Dean admitted. “But I think I’m starting to get an idea.”

“Well, my two cents, for what it’s worth…” Benny set his near-empty bottle on the floor and turned towards Dean. “Wanting a man don’t make you any _less_ of a man.”

On some level, Dean knew that was true. Tomorrow when he woke up, he would still be Dean Winchester, sexy bastard. But even so, this new development was going to take some getting used to.

However, being there with Benny, doing what they were about to do… it was a start. Baby steps.

Dean set down his own bottle. He slid out of his jacket and tossed it onto the other side of the bed, and turned to look at Benny, waiting.

The bed creaked as Benny scooted closer. “Last chance to tuck tail and run,” he playfully mocked.

“Yeah, right,” Dean shot back with a grin, grabbing a handful of Benny’s shirt and snatching him forward.

And there he was, kissing a man for the very first time.

It wasn’t like kissing a woman, obviously. The beard alone was enough to obliterate any similarity. Benny kissed Dean like he had never been kissed before, wasting no time with gentle pecks but instead shoving his tongue right in and taking full advantage of his mouth, igniting a desire in Dean that raced through his body like wildfire and made him so hard that it was almost painful.

They broke apart sometime later, both men gasping for air. Getting naked took too damn long but they finally managed, leaving a mess of bunched up clothing on the floor as they climbed into the bed. Benny’s body was just the way Dean envisioned, a lot of muscle and a little bit of fat, just the right amount of chest hair, and a cock that looked like it was probably going to hurt.

Benny rummaged around on the floor by the head of the bed for a moment and then popped back up with a condom and a bottle of lube. He set them aside, out of the way but not out of reach, and turned his attention back to Dean, easing his weight on top of him and grinding away at him, hard and slow and desperate.

Dean didn’t know what would drive him to ruin quicker, the way that Benny was kissing him or the way that Benny’s cock was sliding against his in a growing patch of their combined dampness. He moaned into Benny’s mouth and wrapped his arms and legs around him, arching his back and bucking his hips, eager for more of that brain-melting friction.

Benny had to practically pry him loose to get where he needed to go, kissing and licking a wet trail down Dean’s body en route to his destination. Dean knew he must have looked a sight, trying to rub himself on every part of Benny’s body that passed along his dick, but he was way too turned on to give a damn and he was pretty sure that Benny didn’t mind one bit.

As good as Benny’s mouth had felt when they kissed, it felt even better between his legs. Dean cursed a blue streak at the ceiling when Benny’s lips wrapped around him, and when his tongue proceeded to do all sorts of fucking lovely things, Dean was pretty sure that he was going to explode.

“Now, now. Settle down,” Benny purred, following with a teasing lick over the tip of Dean’s cock.

“Well, fuck,” Dean growled, glaring at him. “What the hell did you expect after all of that?”

With a coy smile, Benny sat up on his knees and grabbed the bottle of lube. Dean watched him closely with his legs parted wide, trying to mentally prepare himself for what was about to happen next.

It wasn’t the first time that he ever had a finger up his ass. Some of his ex-girlfriends had been more than willing to oblige him like that. Benny’s finger was thicker and Dean clenched his teeth as the man gingerly worked in another. But any discomfort he felt was soon negated when a lube-slicked digit touched upon a place that made him whimper embarrassingly. Dean closed his eyes and thrust his hips, rocking against Benny’s hand as fingers stretched him open, until Benny deemed him ready and pulled them out.

He heard the sound of the condom wrapper being torn open, and glanced down just in time to see Benny rolling it on. Their eyes locked one last time as Benny grabbed him by the legs and pulled him down in the bed. He pushed forward, pressing against him… and then _into_ him… and Dean seized him by the arms as he tried to ride out the pain. Benny was big and thick and fuck, did it ever hurt like hell.

“Dean?”

“I’m alright,” Dean insisted shakily. After a minute, he loosened his grip on Benny’s arms. “I’m alright,” he said again. And it was just as well because he could see that Benny was having a hard time keeping it together.

They started slowly, building up the pace. For Dean’s part, the pain was still there, and he knew he was going to be all kinds of sore come morning. But there was pleasure there, too, just beyond the hurt, and Dean locked his legs around Benny and chased it with each snap of his hips, his cock rubbing up against Benny’s abdomen, making it wet.

Benny leaned down and kissed him again, grunting into his mouth with each thrust. Dean held onto him tightly as his movements became increasingly erratic. He could feel Benny coming undone and it excited him in ways he never thought possible, knowing that _he_ was the reason that the other man was fast unraveling.

“Dean,” Benny whispered in warning after breaking their kiss, lowering his head onto Dean’s shoulder, his beard scraping him along the cheek.

He pushed back on one arm and used the other to reach between them. Dean shuddered as a possessive hand took him in its grip and stroked him with a purpose.

_“Oh, fuck yeah.”_

Dean grabbed Benny by the wrist, not to slow him down but to keep him from stopping. He could feel himself slipping, like a man dangling over the edge of an abyss with no hope for escape, and when that all too familiar heat uncoiled deep inside him, Dean had no choice but to surrender to it and let it consume him. He came hard, so very hard, his cock spasming in Benny’s hand and spurting sticky and hot all over their stomachs.

With no more reason to hold back, Benny let go of Dean and began pounding into him. Dean gripped the edges of the creaking bed and held on for dear life until Benny gave one last, brutal thrust and froze above him, groaning into his neck.

It took a while before Benny felt capable of moving, which was just fine by Dean since he knew that he wasn’t going anywhere anytime soon. Eventually, Benny rolled off of him and discarded the condom. He then flopped down on his side next to Dean with a satisfied sigh.

“Damn.”

Dean thought back to their earlier encounter in the bathroom at Purgatory.

“You’re welcome,” he replied with a tired yet cheeky smile.

The two men chuckled, which somehow, but quite naturally, led to a slow and drawn out kiss.

Later, long after Benny had cleaned up and dressed and hopped back into bed with a beer, Dean managed to haul himself up and hobble into the bathroom to shower. He came back to the small room to find a beer waiting for him, and the two men made small talk until Dean started yawning.

Benny turned off the light and they settled beneath the blanket. Dean thought that perhaps he should have been at least slightly put-off by sharing a bed with a man he hardly knew, especially given his usual inclination to fuck and run. But he wasn’t. Not at all. And he was okay with that.

Dean had a feeling that he was going to be okay with a lot of things, moving forward.

*****

“How’s your ass?”

Dean laughed as he put on his jacket. “Fuck you, man,” he grumbled to Benny, punctuating the request with a middle finger.

Benny smiled at Dean’s feigned surliness. He stood up from the bed and met him in the center of the room.

“Oh yeah, before I forget,” he said, reaching into his pocket. “I was gonna give it to you last night. Before things played out the way they did.”

Dean stared at the folded scrap of paper being offered to him before slowly accepting it.

“Calm down, I’m not asking you to marry me.”

“No, it’s not that.” Dean looked at the phone number written in Benny’s god-awful chickenscratch and wisely lacking an accompanying name, a grin spreading on his face. “I was just trying to figure out a way to give you _my_ number before I left without being all girly about it.”

“Well... if you ever decide to give me a call, then I’ll have it.”

Benny extended his hand.

“Drive safe, brother.”

Dean shook Benny’s hand… and then pulled him close and kissed him for good measure.

“I’ll see ya.”

He walked outside, squinting into the early morning light. A dull ache down below reminded him that he was in for fifty miles of not so much fun and excitement, but sore ass aside, he had every intention of enjoying the ride. He did what he had set out to do and found out what he needed to know. The fire that Dean had tried to fight wasn’t so much extinguished as it was burning steadily now, a part of him that he could no longer try to deny.

Even if he never came right out and called it by name, the important thing was that he _knew_. That was good enough for him.

Dean got into his car, wincing and shifting about until he found a way of sitting that didn’t bug him quite so much. Then he started it and took off, making his way towards the highway that would lead him home. He cranked up the music and hit the gas, with the sun in his eyes and a smile on his face.

He had gotten laid. Spectacularly.

And by the looks of things, he had also made a new friend.

Quite possibly, a _good_ friend.

All in all, not a bad night.


End file.
